Trimethyl borate-induced one-pot homologation reactions of isoquinoline with di- tert-butyl-TMP zincate

Trimethyl borate-induced one-pot homologation reactions of isoquinoline with di- tert-butyl-TMP zincate

Novel one-pot homologation reactions of isoquinoline and quinoline with di- tert-butyl-TMP zincate/trimethyl borate are described. 1- tert-Butyl-3,4-dihydroisoquinoline 1 and 1- tert-butylisoquinoline 2 are formed unexpectedly under the presented reaction conditions with relative ease. A reaction me...

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Veröffentlicht in:Tetrahedron letters 2011-07, Vol.52 (29), p.3747-3750
Hauptverfasser: Seo, Hye Ji, Yoon, Soo Jung, Jang, So Hyun, Namgoong, Sung Keon
Format: Artikel
Sprache:eng
Schlagworte:
1,2-Migration
Aptitude
Borates
Chemistry
Di- tert-butyl-TMP zincate
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Homologation
Homology
Isoquinoline
Kinetics and mechanisms
Ligands
Organic chemistry
Preparations and properties
Quinoline
Reaction mechanisms
Reactivity and mechanisms
Tetrahedrons
Trimethyl borate
Zincates
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Zusammenfassung:Novel one-pot homologation reactions of isoquinoline and quinoline with di- tert-butyl-TMP zincate/trimethyl borate are described. 1- tert-Butyl-3,4-dihydroisoquinoline 1 and 1- tert-butylisoquinoline 2 are formed unexpectedly under the presented reaction conditions with relative ease. A reaction mechanism, including 1,2-migration of the tert-butyl group from 1-isoquinolylzincate, is proposed in detail. Migratory aptitudes of other ligands of isoquinolyl zincates are also discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.05.045